Radical-based route to 2-(trifluoromethyl)-1,3,4-oxadiazoles and trifluoromethyl-substituted polycyclic 1,2,4-triazoles and dihydrofurans.

Ling Qin 1 Samir Z Zard 1
1 DCSO - Laboratoire de synthèse organique
Abstract : O-Ethyl S-[5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl]methyl xanthate was readily prepared on a large scale and shown to undergo very efficient intermolecular radical additions to unactivated alkenes. The products were further elaborated by exploiting both radical and ionic processes to provide a variety of trifluoromethyl-substituted derivatives, including medicinally relevant triazoles. In particular, the application of a radical allylation on the initial adducts leads to structures that are able to undergo intramolecular [4 + 2] cycloaddition reactions.
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https://hal-polytechnique.archives-ouvertes.fr/hal-01152227
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Submitted on : Friday, May 15, 2015 - 3:45:23 PM
Last modification on : Thursday, February 7, 2019 - 5:16:40 PM

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Ling Qin, Samir Z Zard. Radical-based route to 2-(trifluoromethyl)-1,3,4-oxadiazoles and trifluoromethyl-substituted polycyclic 1,2,4-triazoles and dihydrofurans.. Organic Letters, American Chemical Society, 2015, 17 (6), pp.1577-80. ⟨10.1021/acs.orglett.5b00457⟩. ⟨hal-01152227⟩

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